I've read the suggestions to deal with the issue of Outlook 2013 not sending automatically but sending just fine when pressing F9--that is until one of the (Microsoft) engineers told me to disable "Include group in Send/Receive". In that case, nothing got sent no matter what I clicked.
So this was working. It's not now. I have rebuilt the accounts (several times) and it still fails. I'm about done with Outlook after having used it since it first appeared decades ago. If it does not know how to manage a simple IMAP GMAIL account then why bother with it?
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William Vaughn
Author, Mentor, Trainer, MVP
Beta V Corporation
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